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Keely's family have played League of Ireland football at various levels. His late father Peter Keely played for Shelbourne, his brother Joe played on the same Home FarmFAI Cup winning side of 1975 as Dermot Keely himself. And his son Alan Keely also played in the League of Ireland.

He then moved to Dundalk where he made his debut against Shamrock Rovers in September 1978. In his first season the Co. Louth outfit won the domestic double. In 1981 Keely captained Dundalk to win the FAI Cup. The League Cup was also won this season.

Keely's time with Dundalk and Glentoran saw him play in notable European Cup ties. In 1979, Dundalk reached the second round of the 1979–80 European Cup and were drawn with Celtic. The first leg saw Dundalk produce a notable display to come away with a 3–2 defeat at Parkhead. In the return leg in front of a packed Oriel Park with Keely as captain, Dundalk missed a last-minute opportunity to win the tie on away goals and the game finished 0–0 [3]. This is regarded as one of the best performances by a League of Ireland club in European competition.

Two years later, Keely played his part in Glentoran's run to the second round of the European Cup. In the first leg against CSKA Sofia, they lost 2–0. However, the return leg saw Glentoran take a 2–0 lead, forcing the game into extra time. With only five minutes remaining, CSKA scored the goal they needed. The tie finished 3–2 on aggregate, which had been the closest Glentoran came to reaching the last eight of European competition since 1974.[2]

Keely's first managerial job was as UCD player-manager.[1] However after just two months at Belfield Jim McLaughlin (football manager) persuaded Keely to sign for Shamrock Rovers. He made his debut against Athlone Town in November 1983. He scored his first goal for Rovers in a 3–2 defeat to Shelbourne at Harold's Cross on 11 December 1983. When McLaughlin left at the end of the 1985/86 season to manage his home club Derry City Dermot was appointed player-manager on 16 May.

In the 1986/87 season, Rovers owners controversially announced the sale of Glenmalure Park near the end of season. However, Rovers won another double in this their final season at Milltown to bring Keely's Rovers haul to 4 League championships and 3 FAI Cups.

The 1987/88 season started with Rovers controversially playing at Tolka Park. Rovers fans boycotted the ground en masse. Every game was picketed and with the crowds practically gone the team invariably suffered. Keely was quoted years later as saying:

“

I didn't realise the depth of feeling about Glenmalure Park and all I wanted to do was win the League for Shamrock Rovers.

He then took over as manager of Sligo Rovers in 1989 and achieved promotion in his first season. He guided Sligo Rovers to their highest Premier Division place in a decade in the 1990/91 season by finishing 5th.

In the calendar year 1996 Keely managed four clubs: Dundalk, Finn Harps, Athlone Town and Home Farm.

He took over as manager of Shelbourne in July 1998 [4] and won two championships (1999–2000 and 2001–02) and one FAI Cup (2000) in his time at Tolka Park. He also guided Shels to victory over Macedonian side Sloga Jugomagnat in the first round of the 2000–01 UEFA Champions League qualifiers. Shels 1–0 win in the first leg in Skopje was the first away win for a League of Ireland side in any UEFA competitions for eighteen years.

Keely then became the first manager of new league club Kildare County in 2002. After a credible 5th place finish he then walked out to manage Derry City lasting only 3 months[5]

After a spell out of the game he then took over at Dublin City.[6] He then took over the management position at Shelbourne FC in 2007 and in his first season back finished fifth in the first division. In his second season in charge, Shelbourne lead the division going into the final game, and needed a home win against mid-table Limerick to gain promotion, but were denied by a 92nd-minute equaliser, and so were overhauled by Dundalk, who won away to Kildare County. On 27 May 2010, Keely stepped down as manager of Shelbourne to become Shelbourne's youth team manager and community development officer.[7]